Emanuel talks about his darkest days at Clinton White House

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It wasn’t always all smiles for these three. Chicago Mayor Rahm Emanuel (center), shown with his wife, Amy Rule, and former President Bill Clinton, recalled how he was nearly fired while working in the Clinton White House — just as Rule, then in girlfriend, was moving to join him in Washington. | Getty Images

Mayor Rahm Emanuel on Wednesday advised employees at a fast-growing Chicago start-up to “learn from failure” — then told the story of how he rebounded after his lowest moment in politics.

It’s widely known that, as a brash young staffer to former President Bill Clinton, Emanuel was demoted and nearly fired at the behest of then-first lady Hillary Clinton.

The mayor has even joked openly about having been fired, but refusing to leave.

But during a fireside chat at Shiftgig’s new offices in the Loop, Emanuel put a lot more meat on the bone.

He talked about the unfortunate timing of the firing and how it came just after he had convinced his then-girlfriend and now wife, Amy Rule, to join him in Washington and buy a condo together.

“I know you find it hard to believe, but I mouthed off one too many times to the wrong people. She arrived the day we actually bought a condo together. And I was being told by the chief of staff, `You’re out of here,’” Emanuel said.

“You convince somebody to leave their life, move to be part of your life and I lost my job in the first six months. It’s a real talent to do. I lost everything I was working for my whole professional life to get to — plus.”

Emanuel said he has no idea “where I found the gumption,” but he told the chief of staff, “I’m not leaving until the president of the United States tells me I’m gone.”

With that, Emanuel said he was moved to “an office with a Playskool phone that didn’t dial out” and assigned an impossible task that turned out to be possible after all: to pass the North American Free Trade Agreement.

“We had three votes. It was like zero. And I worked my way [to passage]. I then took over and passed the assault weapons ban and did a number of other discreet projects that nobody wanted to touch. And when he got re-elected, he asked me to become senior adviser,” the mayor said.

“The biggest lesson was to know how to take failure, learn something out of it, dust yourself off, then put one foot in front of the other. …Your life lesson will come from failure — not from your success. And how you take that. It’s hard. But, learn something from it. Pick yourself up. Put your right foot in front of your left and keep going. Do something better.”

Emanuel said the lesson he learned at the Clinton White House is particularly appropriate for a company like Shiftgig, a mobile technology platform that connects businesses with hourly workers.

The company’s new office at 1 N. State St. is designed to support plans to add 100 employees this year.

But Emanuel warned that the good times won’t always be rolling.

“You guys are a start-up. You’re going to stumble every day. You’re gonna stumble your way to success. The key thing, as a team, is to figure out how to learn from it,” the mayor said.

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